2-Methoxy-5-nitrobenzoic acid → 5-Amino-2-methoxybenzoic acid

HRID 1253253Notes

Reaction equation

HRID 1253253 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].Cl.O1CCOCC1>C(O)(=O)C.[Zn]>[NH2:12][C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 2841632-Methoxy-5-nitrobenzoic acidHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 135492445-Amino-2-methoxybenzoic acidYield 290.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
30 °C

Procedure

Cycloartenyl ester of 2-methoxy-5-nitrobenzoic acid (34.0 g, 0.056 mole) prepared according to the procedure of Example 170 was suspended in acetic acid (1.2 l) at 20° C., and thereto 6N-HCl-dioxane (19 ml, 2 equivalent) and zinc powder (68 g) were added. The mixture was stirred at 30° C. for 1 hour. Then, zinc powder was removed by filtration, and the filtrate was concentrated under reduced pressure and the residue was extracted with chloroform. The chloroform extracts were washed successively with water and saturated aqueous NaHCO3 solution, then dried, concentrated, and the residual crystals were recrystallized from methylene chloride-hexane (1:4, v/v), giving cycloartenyl ester of 5-amino-2-methoxybenzoic acid (27.2 g) in a 84.4% yield. m.p. 180°-182° C.

Workup

  1. customThen, zinc powder was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. extractionthe residue was extracted with chloroform
  4. washThe chloroform extracts were washed successively with water and saturated aqueous NaHCO3 solution
  5. customdried
  6. concentrationconcentrated
  7. customthe residual crystals were recrystallized from methylene chloride-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-e3f942c555424081be85f3ce332555c5
Source dataset
uspto-grants-1988_05
Patent number
US04748161

Reaction notes

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